EP1860168A2 - Feuille adhésive sensible à la pression - Google Patents

Feuille adhésive sensible à la pression Download PDF

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Publication number
EP1860168A2
EP1860168A2 EP07010260A EP07010260A EP1860168A2 EP 1860168 A2 EP1860168 A2 EP 1860168A2 EP 07010260 A EP07010260 A EP 07010260A EP 07010260 A EP07010260 A EP 07010260A EP 1860168 A2 EP1860168 A2 EP 1860168A2
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EP
European Patent Office
Prior art keywords
pressure
sensitive adhesive
adhesive sheet
layer
base material
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP07010260A
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German (de)
English (en)
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EP1860168A3 (fr
Inventor
Yuji Okawa
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Nitto Denko Corp
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Nitto Denko Corp
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Publication date
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Publication of EP1860168A2 publication Critical patent/EP1860168A2/fr
Publication of EP1860168A3 publication Critical patent/EP1860168A3/fr
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/20—Adhesives in the form of films or foils characterised by their carriers
    • C09J7/22—Plastics; Metallised plastics
    • C09J7/24—Plastics; Metallised plastics based on macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C09J7/245—Vinyl resins, e.g. polyvinyl chloride [PVC]
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
    • C09J7/38—Pressure-sensitive adhesives [PSA]
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/40—Adhesives in the form of films or foils characterised by release liners
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
    • C09J2203/326—Applications of adhesives in processes or use of adhesives in the form of films or foils for bonding electronic components such as wafers, chips or semiconductors
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/14—Layer or component removable to expose adhesive
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/28—Web or sheet containing structurally defined element or component and having an adhesive outermost layer
    • Y10T428/2839—Web or sheet containing structurally defined element or component and having an adhesive outermost layer with release or antistick coating

Definitions

  • the present invention relates to a pressure-sensitive adhesive sheet which is usable in processing (such as dicing, expanding, and picking up) products to be processed such as LED parts, electronic parts, semiconductor wafers, resin boards for sealing semiconductor devices, and glass wafers.
  • Pressure-sensitive adhesive sheets have been widely employed in manufacturing semiconductors and so on.
  • protective sheets to be used for protecting semiconductor wafers in the step of back grinding or supporting sheets to be used for supporting (fixing) wafers in the step of cutting (dicing) into elements chips in particular, pressure-sensitive adhesive sheets including soft vinyl chloride as the base material are widely employed since they have high expandability and excellent pick up capability (see, for example, Patent Documents 1 and 2).
  • these pressure-sensitive adhesive sheets frequently have a release film attached thereto or a release layer formed on the back side of the pressure-sensitive adhesive layer thereof.
  • a soft vinyl chloride resin usually contains a compound having a relatively low molecular weight such as a plasticizer or a stabilizer, and such a compound would sometimes move and diffuse in the sheet and separate out on the surface of the pressure-sensitive adhesive layer as a deposit (i.e., the phenomenon called "migration").
  • migration the phenomenon called "migration"
  • the pressure-sensitive adhesive sheet is attached to an article to be processed such as a semiconductor wafer and the pressure-sensitive adhesive sheet is peeled off after the completion of the processing, this deposit sticks to the article as the residue and causes some troubles in the manufacturing or worsens the qualities of the product (i.e., the phenomenon called "transfer contamination").
  • An object of the invention is to prevent a deposition of a plasticizer or the like onto a surface of a pressure-sensitive adhesive layer of a pressure-sensitive adhesive sheet made of a vinyl chloride resin having a high expandability; and to provide a pressure-sensitive adhesive sheet which is usable in processing semiconductor wafers, and the like, while causing little transfer contamination.
  • the inventors conducted intensive studies. As a result, they have found out that the transfer of a fatty acid, an aliphatic metal salt, or the like toward an article to be processed can be prevented by controlling the surface of a release film being in contact with the pressure-sensitive adhesive layer surface of a pressure-sensitive film or the surface of a release layer formed on the opposite side to the pressure-sensitive adhesive layer side (back side) of a pressure-sensitive adhesive sheet to have a specific surface free energy without forming an intermediate layer for preventing the migration of a low-molecular weight compound, thereby completing the invention.
  • the present invention relates to the followings.
  • the pressure-sensitive adhesive sheet for holding wafers according to the invention has a high expandability, picking up can be easily executed and thus defective products can be reduced. Moreover, it is industrially advantageous because of causing little transfer contamination on chip surface and thus contributing to an increase in productivity.
  • Fig. 1 is a schematic section view which shows one embodiment of the pressure-sensitive adhesive sheet according to the invention.
  • a release film 7 is temporarily attached to a pressure-sensitive adhesive film 4.
  • the pressure-sensitive adhesive sheet is used after peeling off the release film 7.
  • the pressure-sensitive adhesive film 4 has a pressure-sensitive adhesive layer 3 formed on the surface of the base material layer 2 to which the release film 7 is to be attached.
  • the release film 7 has a release layer 5 formed on at least one surface of a liner base material 6.
  • Fig. 2 shows another embodiment of the present invention.
  • a pressure-sensitive adhesive sheet 8 shown in Fig. 2 a pressure-sensitive adhesive layer 11 is formed on one surface of the base material layer 10, and a release layer 9 is formed on the other surface of the base material layer 10 which is opposite to the surface on which the pressure-sensitive adhesive layer 11 is formed.
  • the pressure-sensitive adhesive sheet according to the invention has a structure in which a release film having a release layer is laminated on (attached to) a pressure-sensitive adhesive film having a base material layer and a pressure-sensitive adhesive layer, or a structure which includes a base material layer, a pressure-sensitive adhesive layer and a release layer without attaching a release film thereto.
  • a release film having a release layer is laminated on (attached to) a pressure-sensitive adhesive film having a base material layer and a pressure-sensitive adhesive layer
  • a structure which includes a base material layer, a pressure-sensitive adhesive layer and a release layer without attaching a release film thereto In the case where neither a release layer nor a release film is provided, the advantage of the invention cannot be established.
  • the matter having the release film attached thereto is called "a pressure-sensitive adhesive sheet" while one from which the release film has been peeled off is called “a pressure-sensitive adhesive film” for the purpose of distinction.
  • a sheet having the above-described structure in which the release film is laminated is favorable, since the pressure-sensitive adhesive surface can be protected from contamination or adhesion of foreign matters when it is once wound into a roll and then rewound for examining the appearance in the inspection process.
  • the release film is peeled off before attaching.
  • a structure without using a release film may be employed. In this case, however, a release layer should be formed on the back side of the pressure-sensitive adhesive layer to prevent the sticking of the front and back sides of the sheet and to facilitate the winding off of the sheet when the pressure-sensitive adhesive sheet is wound off from a roll.
  • the base material layer is constituted of a soft polyvinyl chloride film. It is preferable to use a soft polyvinyl chloride resin as the base material layer, since a high expandability can be obtained so that picking up can be easily conducted.
  • the soft polyvinyl chloride resin may be either a resin containing a plasticizer or a copolymer or a polymer alloy.
  • the plasticizer include a phthalic acid ester, an adipic acid ester, a sebacic acid ester, other polyester plasticizers, an epoxy-based plasticizer such as epoxidized soybean oil and a trimet-based plasticizer.
  • a plasticizer although the amount thereof is not restricted, it is preferably added in an amount of from 1 to 55 parts by weight, more preferably from 3 to 45 parts by weight, based on 100 parts by weight of the polyvinyl chloride polymer employed in the base material layer. In the case where the plasticizer is added in an amount less than 1 part by weight, the polyvinyl chloride resin becomes hard and the expandability is lowered in some cases.
  • Examples of the above-described phthalic acid ester include dibutyl phthalate (DBP), di-normal-octyl phthalate (DnOP), dinonyl phthalate (DNP), diiononyl phthalate (DINP), diisodecyl phthalate (DIDP), di-2-ethylhexyl phthalate (DEHP), diethyl phthalate (DEP), dicyclohexyl phthalate (DCHP), dipropyl phthalate (DprP), dihexyl phthalate (DHP), dipentyl phthalate (DPP) and butylbenzyl phthalate (BBP).
  • DBP dibutyl phthalate
  • DnOP di-normal-octyl phthalate
  • DNP dinonyl phthalate
  • DINP diiononyl phthalate
  • DIDP diisodecyl phthalate
  • DEHP di-2-ethyl
  • Examples of the above-described adipic acid ester include dioctyl adipate (DOA), diisononyl adipate (DINA), di-normal-alkyl adipates and dialkyl adipates.
  • Examples of the above-described sebacic acid esters include dibutyl sebacate (DBS) and dioctyl sebacate (DOS).
  • Examples of the above-described copolymer include vinyl chloride copolymers such as urethane-vinyl chloride copolymer, ethylene-vinyl chloride copolymer, vinyl acetate-vinyl chloride copolymer and ethylene-vinyl acetate copolymer. Either one of these copolymers, a mixture of two or more thereof or a mixture thereof with another resin or elastomer may be used. Needless to say, the above-described copolymer includes a graft copolymer as well as a block copolymer and a random copolymer. The above-described mixtures include not only a mere blend but also an alloy having a chemical bond.
  • the base material layer of the invention may further contain other known additives as, for example, a stabilizer, an antioxidant, a lubricant or a processing aid, so long as the advantage of the invention is not deteriorated thereby.
  • the base material layer of the invention contains at least one compound selected from the group consisting of a fatty acid compound, an aliphatic metal salt and a phosphoric acid ester.
  • a fatty acid compound as described above include a fatty acid, a fatty acid ester and a fatty acid amide. These compounds have been generally employed as a plasticizer, a stabilizer, a surfactant, a lubricant, a processing aid or the like. Such a compound contained in the base material layer bleeds out onto the surface of the pressure-sensitive adhesive layer during storage and, in particular at a low temperature, forms a solid deposit.
  • the content of the plasticizer including at least one compound selected from the group consisting of a fatty acid compound, an aliphatic metal salt and a phosphoric acid ester as described above is not particularly restricted, the content thereof preferably ranges from 20 to 40 parts by weight based on 100 parts by weight of the polyvinyl chloride resin in the base material layer.
  • the content of a stabilizer preferably ranges from 0.5 to 5 parts by weight. In the case where the content of the plasticizer or the stabilizer is less than the lower limit as defined above, only little effect can be obtained in some cases. In the case where the content thereof exceeds the upper limit, on the other hand, such an additive is liable to bleed out on the surface in some cases.
  • thickness of the base material layer of the invention is not particularly restricted, it is preferably from 50 to 250 ⁇ m, more preferably from 60 to 230 ⁇ m.
  • the thickness is less than 50 ⁇ m, the whole pressure-sensitive adhesive sheet becomes less "elastic" and thus the wafer-holding power is lowered in the dicing step. As a result, the dicing processability is worsened or chipping occurs in some cases. From the viewpoints of transfer properties, handling properties, cost, etc., it is also undesirable that the thickness is more than 250 ⁇ m.
  • the breaking elongation of the film to be used as the base material layer of the invention is preferably from 150 to 500%, more preferably from 180 to 400%.
  • a release agent may be added to the base material layer.
  • the release agent bleeds out on the surface and thus a layer of the release agent (release layer) is formed on the surface opposite to the pressure-sensitive adhesive layer side.
  • the release agent may be applied to the base material layer, as well as adding the release agent to the base material layer.
  • the amount thereof to be added is not particularly restricted, it is preferably from 0.3 to 1.5 parts by weight based on 100 parts by weight of the polyvinyl chloride resin in the base material layer.
  • the amount of the release agent is less than 0.3 part by weight, the release agent layer cannot be sufficiently formed on the surface and thus the releasing effect is lowered.
  • the content thereof exceeds 1.5 parts by weight, it is sometimes observed that an excessive releasing effect is achieved and thus the surface free energy can be hardly controlled within the range as specified in the invention in some cases.
  • the kind of the release agent to be used in the invention is not restricted so long as it satisfies the requirement for surface free energy according to the invention.
  • a conventional release agent may be used.
  • a compound having a long-chain alkyl group carrying 10 or more carbon atoms may be mentioned as a preferable example thereof from the viewpoints of releasability and prevention of the bleeding out of a low-molecular weight compound from the pressure-sensitive adhesive.
  • Specific examples thereof include synthetic waxes, for example, coal-based synthetic waxes such as montan wax, polyethylene waxes and fat-based synthetic waxes such as a fatty acid amide and a fatty acid ester and crosslinked polymers having a long-chain alkyl group. More specifically, there can be mentioned a product of a reaction between octadecyl isocyanate and polyvinyl alcohol, methylenebis stearic acid amide, ethylene-vinyl carbide copolymer and so on.
  • a release agent is to be mixed with vinyl chloride
  • methylenebis stearic acid amide and a mixture thereof (a mixture with a fatty acid amide, etc.) are preferred.
  • the release agent is a polymer or a crosslinked compound.
  • a product of a reaction between octadecyl isocyanate and polyvinyl alcohol and an ethylene-vinyl octadecyl carbide copolymer are preferred.
  • a fluorinated release agent or a silicone-based release agent is not preferable since they have a low surface free energy.
  • conventional pressure-sensitive adhesives such as rubber-based, acrylic, silicone-based or vinyl ester-based pressure-sensitive adhesives may be used.
  • an acrylic pressure-sensitive adhesive it is preferable to use an acrylic pressure-sensitive adhesive.
  • the rubber-based pressure-sensitive adhesives include pressure-sensitive adhesives containing, as the base polymer, natural rubber or various synthetic rubbers (for example, polyisoprene rubber, styrene-butadiene (SB) rubber, styrene-isoprene (SI) rubber, styrene-isoprene-styrene block copolymer (SIS) rubber, styrene-butadiene-styrene block copolymer (SBS) rubber, styrene-ethylene-butylene-styrene block copolymer (SEBS) rubber, styrene-ethylene-propylene-styrene block copolymer (SEPS) rubber, styrene-ethylene-propylene block copolymer (SEP), regenerated rubber, butyl rubber, polyisobutylene and modified rubber products thereof).
  • SB polyisoprene rubber
  • SB styren
  • An acrylic pressure-sensitive adhesive contains an alkyl acrylate and/or an alkyl methacrylate (hereinafter referred to as alkyl (meth)acrylate) as the principle constituting monomer. Although it may be a homopolymer composed of a single monomer component, it is usually a copolymer of two or more monomer components (that is called an alkyl (meth)acrylate copolymer). Such an alkyl (meth)acrylate copolymer may be either a copolymer composed of two or more alkyl (meth)acrylates exclusively as the monomer components or a copolymer composed of one or more alkyl (meth)acrylates together with other copolymerizable component(s).
  • the acrylic pressure-sensitive adhesive may be a mixture of two or more different alkyl (meth)acrylate copolymers.
  • alkyl (meth)acrylate monomer unit in the invention examples include acrylic acid and methacrylic acid esters of linear or branched alkyl group having 30 or less (in particular, from 4 to 18) carbon atoms such as a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, a t-butyl group, an isobutyl group, an amyl group, an isoamyl group, a hexyl group, a heptyl group, a cyclohexyl group, a 2-ethylhexyl group, an octyl group, an isooctyl group, a nonyl group, an isononyl group, a decyl group, an isodecyl group, an undecyl group, a lauryl group, a tridecyl group, a tetradecyl group,
  • Examples of other copolymerizable monomer unit(s) include carboxyl group-containing monomers such as acrylic acid, methacrylic acid, carboxyethyl acrylate, carboxypentyl acrylate, itaconic acid, maleic acid, fumaric acid and crotonic acid; acid anhydride monomers such as maleic anhydride and itaconic anhydride; hydroxyl group-containing monomers such as 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 6-hydroxyhexyl (meth)acrylate, 8-hydroxyoctyl (meth)acrylate, 10-hydroxydecyl (meth)acrylate, 12-hydroxylauryl (meth)acrylate and (4-hydroxymethylcyclohexyl)-methylacrylate; sulfonate group-containing monomers such as styrenesulfonic acid, allylsulfonic acid, 2-(meth)acrylamide
  • examples of the polyfunctional monomer component include hexanediol (meth)acrylate, (poly)ethylene glycol di(meth)acrylate, (poly)propylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, pentaerythritol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, dipentaerythritol hexa(meth)acrylate, epoxy acrylate, polyester acrylate, and urethane acrylate. From the viewpoint of the pressure-sensitive adhesive properties, etc., it is preferable to use the polyfunctional monomer in an amount of 30% by weight or less based on the total monomer components.
  • the weight-average molecular weight of the acrylic resin to be used as the acrylic pressure-sensitive adhesive in the pressure-sensitive adhesive layer of the invention is preferably 200,000 or more, more preferably from 300,000 to 2,000,000 and more preferably from 500,000 to 1,500,000. From the viewpoint of exhibiting pressure-sensitive adhesiveness at room temperature (23°C), the glass transition temperature of the acrylic resin in the pressure-sensitive adhesive layer is preferably 0°C or lower, more preferably from -100 to -20°C.
  • the pressure-sensitive adhesive layer of the invention may be either a pressure-sensitive adhesive layer of the radiation polymerization type in which the pressure-sensitive adhesiveness thereof is lowered by radiation irradiation, or a pressure-sensitive adhesive layer of the heat polymerization type in which the pressure-sensitive adhesiveness thereof is lowered by heating.
  • a pressure-sensitive adhesive layer of the radiation polymerization type requires expandability in many cases. Therefore, the advantage of the invention can be more remarkably achieved in the case where the pressure-sensitive adhesive layer is a pressure-sensitive adhesive layer of the radiation-curing type.
  • the pressure-sensitive adhesive layer of the invention is a pressure-sensitive adhesive layer of the radiation polymerization type
  • a radiation polymerizable compound it is preferable to add a radiation polymerizable compound to the pressure-sensitive adhesive layer.
  • the radiation polymerizable compound use may be made of a low-molecular weight compound having at least two photopolymerizable carbon-carbon double bonds per molecule that is disclosed by, for example, JP-A-60-196956 and JP-A-60-223139 .
  • Examples of the radiation polymerizable compound include esters of (meth)acrylic acid with polyhydric alcohols such as trimethylolpropane tri (meth)acrylate, tetramethylolmethane tetra(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol monohydroxypenta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, 1,4-butylene glycol di(meth)acrylate, and 1,6-hexanediol di(meth)acrylate.
  • esters of (meth)acrylic acid with polyhydric alcohols such as trimethylolpropane tri (meth)acrylate, tetramethylolmethane tetra(meth)acrylate, pentaerythritol tri(meth)acrylate, penta
  • an ester acrylate oligomer isocyanurate or isocyanurate compounds such as 2-propenyl-3-butenyl cyanurate and tris(2-methacryloxyethyl) isocyanurate and an urethane acrylate-based oligomer.
  • an urethane acrylate-based oligomer having a weight-average molecular weight of from 100 to 40000 (preferably from 200 to 30000) makes it possible to considerably improve the performance of preventing transfer contamination and remarkably reduce the sticking of the pressure-sensitive adhesiveness to the chip surface in the picking up step. Either one of these radiation polymerizable compounds or a mixture of two or more thereof may be used.
  • the amount of the radiation polymerizable compound is not particularly restricted, from the viewpoint of re-releasability (picking up performance) after the radiation irradiation, it is preferable to add the radiation polymerizable compound in an amount of from 30 to 75% by weight, more preferably from 40 to 70% by weight, based on the total pressure-sensitive adhesive layer.
  • an acrylic resin having a carbon-carbon double bond in the side chain, midway of the main chain or at the terminus of the main chain may be used as a substitute for the radiation polymerizable compound as described above or in addition thereto.
  • an alkyl (meth)acrylate copolymer having a carbon-carbon double bond in its molecule can be obtained by introducing a carbon-carbon double bond into an alkyl (meth)acrylate copolymer as described above.
  • this compound can be prepared by various known methods, it is preferable from the viewpoint of easiness in molecular design to employ a method which includes preliminarily copolymerizing a polymer with a monomer having a functional group, and then conducting an addition reaction with a monomer, which has another functional group capable of reacting with the above-described functional group and a carbon-carbon double bond, while maintaining the carbon-carbon double bond.
  • the combination of the functional group in the acrylic polymer with the functional group in the monomer having the carbon-carbon double bond include a carbonate group with an epoxy group or an aziridyl group, and a hydroxyl group with an isocyanate group, and so on.
  • a combination of a hydroxyl group as the functional group in the acrylic polymer with an isocyanate group as the functional group in the monomer is particularly preferable, since the reaction can be easily followed in this case.
  • the isocyanate compound having a carbon-carbon double bond include methacryloyloxy isocyanate and 2-methacryloyloxyethyl isocyanate.
  • acrylic polymer examples include polymers carrying, as a monomer unit, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 6-hydroxyhexyl (meth)acrylate, 2-hydroxyethyl vinyl ether, 4-hydroxybutyl vinyl ether, diethylene glycol monovinyl ether and so on.
  • the acrylic resin has the carbon-carbon double bond in a side chain
  • the ratio of side chains having the carbon-carbon double bond is less than 1% based on the total side chains, only little effect can be established by introducing the carbon-carbon double bond into the side chains.
  • the pressure-sensitive adhesive layer of the invention contains a photopolymerization initiator.
  • the photopolymerization initiator include benzoin alkyl ethers such as benzoin methyl ether, benzoin propyl ether, benzoin isopropyl ether and benzoin isobutyl ether; aromatic ketones such as benzyl, benzoin, benzophenone and ⁇ -hydroxycyclohexyl phenyl ketone; aromatic ketals such as benzyl dimethyl ketal; and thioxanthones such as polyvinyl benzophenone, chlorothioxanthone, dodecyl thioxanthone, dimethyl thioxanthone and diethyl thioxantone.
  • the photopolymerization initiator may be added in an arbitrary amount without restriction, it is added preferably in an amount of from 0.1 to 12 parts by weight, more preferably from 0.5 to 10 parts by weight, based on 100 parts by weight of the acrylic resin constituting the pressure-sensitive adhesive layer.
  • the content of the photopolymerization initiator is less than 0.1 part by weight, the re-releasability due to radiation irradiation becomes insufficient in some cases.
  • the photopolymerization initiator sometimes bleeds out on the pressure-sensitive adhesive layer surface and causes transfer contamination of semiconductor wafers.
  • the pressure-sensitive adhesive layer of the invention may further contain various conventional additives such as a tackifier, an antioxidant, a filler, and a colorant, so long as the advantage of the invention is not deteriorated thereby.
  • the thickness of the pressure-sensitive adhesive layer of the invention is preferably from 5 to 20 ⁇ m, more preferably from 5 to 15 ⁇ m. In the case where the thickness exceeds 20 ⁇ m, the aggregation power of the adhesive is sometimes lowered. In the case where the pressure-sensitive adhesive layer thickness is less than 5 ⁇ m, an even pressure-sensitive adhesive layer can be hardly formed or the adhesiveness becomes unstable, which sometimes causes deterioration in the characteristics.
  • the release layer may be formed by adding a release agent to the base material film or applying the release agent thereto.
  • a release agent use may be made of the above-described compounds.
  • the release agent can be applied in the form of a dispersion or solution in an organic solvent.
  • Application may be made of by a known method, for example, the gravure method, the fountain method, the air knife method, the reverse roll method, the dipping method, the calender method or the kiss coating method.
  • the release film has a layered structure in which a release layer is formed on at least one side of a liner base material.
  • the liner base material to be used in the release film is not particularly restricted, and it include films made of synthetic resins such as polyethylene, polypropylene and polyethylene terephthalate.
  • the release layer is the same as described above.
  • the release film in the invention may be subjected to a UV blocking treatment to prevent the pressure-sensitive adhesive layer from the reaction with environmental UV light.
  • the thickness of the release film in the invention is not particularly restricted, it is preferably from 12 to 75 ⁇ m, more preferably from 25 to 50 ⁇ m. In the case where the thickness of the release film exceeds 75 ⁇ m, the film sometimes becomes highly rigid and can be hardly handled. In the case where the thickness is less than 12 ⁇ m, the film sometimes wrinkles because of being too thin.
  • the surface free energy of the surface of the release film which is to be attached to the pressure-sensitive adhesive layer is 20 dyn/cm or more but less than 30 dyn/cm, preferably 20 dyn/cm or more but less than 25 dyn/cm.
  • the surface free energy of the surface of the pressure-sensitive adhesive sheet opposite to the surface on which the pressure-sensitive adhesive layer is formed is 20 dyn/cm or more but less than 30 dyn/cm, preferably 20 dyn/cm or more but less than 25 dyn/cm.
  • the surface free energy is less than 20 dyn/cm, a fatty acid and the like, contained in the base material layer, deposit on the surface of the pressure-sensitive adhesive layer when the pressure-sensitive adhesive sheet is stored in an environment at 15°C or lower.
  • the deposit transfers onto the surface of an adherend such as a semiconductor wafer in the step of attaching the pressure-sensitive adhesive sheet and peeling it, and thus the adherend is contaminated.
  • the surface free energy is more than 30 dyn/cm
  • the peeling force becomes large in the step of peeling the release film from the pressure-sensitive adhesive layer (the step of winding off from a roll in the case of forming no release film) and thus the winding tension of the pressure-sensitive adhesive sheet or the release film is enlarged.
  • the pressure-sensitive adhesive sheet suffers from breakage or peel-off of the pressure-sensitive adhesive layer and thus the workability and productivity are lowered.
  • the present invention has a characteristic that the surface free energy of the release layer surface is controlled within a specific range.
  • a pressure-sensitive adhesive sheet having a release film will be illustrated by way of example. Since this release film has a high surface free energy, there is a high energy barrier in depositing a fatty acid or the like to the interface between the release film and a pressure-sensitive adhesive layer (i.e., there is a high energy barrier in forming a new interface). Thus, the fatty acid or the like diffusing in the pressure-sensitive adhesive sheet can hardly come close to the interface with the release film so that a deposit is formed in only a small amount.
  • a releasing agent having a high affinity for a plasticizer in the vinyl chloride base material is employed to thereby achieve a easy releasability. Accordingly, it becomes possible to impart excellent releasability even though the surface free energy is relatively high.
  • the peeling force (180° peel: determined in accordance with JIS K 6854) between the pressure-sensitive adhesive film and the release film (between the pressure-sensitive adhesive layer surface and the release layer surface in the case of using no release film) of the pressure-sensitive adhesive sheet according to the invention is preferably from 0 to 1.0 (N/50 mm), more preferably from 0 to 0.9 (N/50 mm).
  • the peeling force exceeds 1 (N/50 mm)
  • the shape of the pressure-sensitive adhesive sheet according to the invention may be appropriately determined depending on the purpose of use without restriction.
  • it may be a tape, a label or the like. It is also possible to preliminarily cut and process the pressure-sensitive adhesive sheet into the same shape as a dicing ring.
  • the pressure-sensitive adhesive sheet according to the invention is to be used for holding and reinforcing wafers in processing semiconductor wafers. It is particularly preferable to use the pressure-sensitive adhesive sheet as a wafer-holding sheet in the dicing step.
  • a polyvinyl chloride film to be used as the base material layer of the invention can be produced by using a polyvinyl chloride resin which has been polymerized by an existing polymerization method such as the ethylene dechlorination method or the oxychlorination method. If necessary, the polyvinyl chloride resin may be kneaded together with a plasticizer, a stabilizer, a lubricant, or the like in a Banbury mixer or a mixing roll or with the use of a uniaxial or biaxial extruder to give a polymer.
  • the polymer can be shaped into a sheet by using, for example, the calender method, the T-die method, the tube method or the like.
  • the remainder of the sheet can be recycled into the calender roll.
  • the blending ratio (the recovery ratio) of the recycled polymer is from 0 to about 5%.
  • the pressure-sensitive adhesive layer can be formed by directly coating a pressure-sensitive adhesive composition on the intermediate layer or by using the transfer method as described above.
  • the pressure-sensitive adhesive layer includes a radiation polymerizable acrylic pressure-sensitive adhesive
  • the pressure-sensitive adhesive composition can be produced in accordance with a conventional polymerization method such as the solution polymerization method, the block polymerization method or the emulsion polymerization method. From the viewpoint of easiness in coating the film, for example, use may be made of solution polymerization method.
  • a pressure-sensitive adhesive composition solution can be obtained by dissolving definite amounts of a main monomer component and a copolymerizable monomer component in a solvent such as toluene and copolymerizing these monomer components and, then optionally adding a radiation polymerizable compound, a crosslinking agent and a photopolymerization initiator. Subsequently, the pressure-sensitive adhesive layer is formed by the direct coating method or the transfer method to give a pressure-sensitive adhesive film. It is also possible that a pressure-sensitive adhesive layer is formed on the release film and attached to the surface of the base material layer to thereby directly obtain a pressure-sensitive adhesive sheet having the release film.
  • the liner base material to be used in the release film of the invention can be produced by a conventional production method. Additionally, it is also possible to use a marketed polyethylene terephthalate film or the like. A release agent is dissolved or dispersed in an organic solvent and the coating solution thus prepared is applied to the liner base material as described above by a conventional coating method. Thus, a release film is obtained. Subsequently, the release film thus obtained is attached to a pressure-sensitive adhesive film to obtain a pressure-sensitive adhesive sheet.
  • the release film before attaching to the pressure-sensitive adhesive layer was employed as a test sample (in the case where no release film was used, the pressure-sensitive adhesive sheet before the lamination of the release layer on the pressure-sensitive adhesive layer was employed as a test sample).
  • the measurement conditions were as follows.
  • Example 1 and Comparative Examples 1 and 2 the release film and the pressure-sensitive adhesive film were referred to as respective ends, a 180°C peel test (in accordance with JIS Z 0237) was conducted and the peeling force (the peeling force between the pressure-sensitive adhesive layer side of the pressure-sensitive adhesive film and the release layer side of the release film) was measured.
  • a pressure-sensitive adhesive sheet (or pressure-sensitive adhesive film) sample cut into a width of 20 mm (after peeling the release film in the case of having the release film) was attached to the adherend by using a attaching roller.
  • the pressure-sensitive adhesive sheet was peeled off and the sample surface (the side to which the pressure-sensitive adhesive sheet had been attached) was observed under a stereoscopic microscope (50 x magnification) (the area observed: 100 mm 2 ).
  • a sample showing few transferred matters was evaluated as having good transfer-preventing properties (referred to as A), while one showing much transferred matters was evaluated as having poor transfer-preventing properties (referred to as B).
  • transfer matters of about several ⁇ m or larger were counted per viewing field.
  • a sample showing less than 10 transferred matters can be evaluated as having good transfer contamination-preventing properties (referred to as A), while one showing 10 or more transferred matters can be evaluated as having poor transfer contamination-preventing properties (referred to as B).
  • a soft vinyl chloride base material (thickness: 70 ⁇ m) containing 4% of additives such as a stabilizer including zinc stearate and so on and 26% of dioctyl phthalate (DOP) was shaped into a film by the calender method. After slitting, a 10% portion in the width direction of the film was returned (recovered) into the calender and film formation was continued. A product obtained after producing the film in a length of 5000 m or longer after the initiation of the film formation was employed.
  • additives such as a stabilizer including zinc stearate and so on and 26% of dioctyl phthalate (DOP)
  • the release film obtained above was attached to the surface of the pressure-sensitive adhesive layer in the pressure-sensitive adhesive film by using a roller to obtain a pressure-sensitive adhesive sheet.
  • the pressure-sensitive adhesive sheet thus obtained showed no deposition or transfer onto the adherend. As Table 1 shows, therefore, it was an excellent pressure-sensitive adhesive sheet showing a favorable releasability with scarce transfer.
  • a mounter M-265 manufactured by Nitto Denko Corporation
  • the pressure-sensitive adhesive sheet was attached to the adherend while peeling off the release film. As a result, the release film could be smoothly peeled off and the pressure-sensitive adhesive sheet well attached to the adherend.
  • a pressure-sensitive adhesive film was obtained as in Example 1 but using no release film and applying an octadecyl isocyanate-polyvinyl alcohol copolymer to the back side of the pressure-sensitive adhesive film which is opposite to the pressure-sensitive adhesive layer side with the use of a solvent mixture containing toluene and methyl ethyl ketone (MEK) and using a kiss coater to form a release layer (thickness: 50 nm).
  • MEK methyl ethyl ketone
  • a pressure-sensitive adhesive sheet was formed.
  • Table 1 shows, the surface free energy of the surface of the release layer in this pressure-sensitive adhesive sheet was 24 dyn/cm.
  • the pressure-sensitive adhesive sheet thus obtained showed no deposition or transfer onto the adherend. As Table 1 shows, therefore, it was an excellent pressure-sensitive adhesive sheet showing a favorable releasability with scarce transfer.
  • the pressure-sensitive adhesive sheet was attached to the adherend. As a result, the release layer surface could be smoothly peeled off and the pressure-sensitive adhesive sheet well attached to the adherend.
  • a pressure-sensitive adhesive film (a pressure-sensitive adhesive sheet) was produced as in Example 1 but adding 0.6 part by weight of methylenebis stearic acid amide (methylenebis stearyl amide) as a release agent to the base material layer material. Although the release agent was not applied, the methylenebis stearic acid amide bled out onto the surface of the base material layer which is opposite to the pressure-sensitive adhesive layer side to thereby form a release layer. No release film was employed. As Table 1 shows, the surface free energy of the surface of the release layer in this pressure-sensitive adhesive sheet was 29 dyn/cm.
  • the pressure-sensitive adhesive sheet thus obtained showed no deposition or transfer onto the adherend. As Table 1 shows, therefore, it was an excellent pressure-sensitive adhesive sheet showing a favorable releasability with scarce transfer.
  • the pressure-sensitive adhesive sheet was attached to the adherend. As a result, the release layer surface could be smoothly peeled off and the pressure-sensitive adhesive sheet well attached to the adherend.
  • a polyethylene terephthalate film having a release layer including polydimethylsiloxane was attached as a release film.
  • Table 1 shows, the surface free energy of the surface of this release film which is to be in contact with the pressure-sensitive adhesive layer was 19 dyn/cm.
  • the pressure-sensitive adhesive sheet thus obtained showed transfer of deposits onto the adherend. Thus, it was inferior in the properties of preventing transfer.
  • the deposits were a crystalline compound of fatty acid amide and another crystalline compound containing a stearic acid component.
  • a mounter M-265 manufactured by Nitto Denko Corporation
  • a high releasability of the release film and favorable adhesion to the adherend were obtained.
  • the release film could be smoothly peeled off and the pressure-sensitive adhesive sheet well attached to the adherend.
  • a polyethylene film manufactured by Okura Industrial Co., Ltd., thickness: 70 ⁇ m
  • Table 1 shows, the surface free energy of the surface of this release film which is to be in contact with the pressure-sensitive adhesive layer was 36 dyn/cm.
  • the pressure-sensitive adhesive sheet thus obtained showed no transfer of deposits onto the adherend. However, it showed a large peeling force.
  • the pressure-sensitive adhesive sheet was attached to the adherend while peeling off the release film with the use of a mounter (M-265 manufactured by Nitto Denko Corporation), the release film could not be smoothly peeled off from the adherend and the adhesion to the adherend was poor.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Adhesive Tapes (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Dicing (AREA)
  • Laminated Bodies (AREA)
EP07010260A 2006-05-24 2007-05-23 Feuille adhésive sensible à la pression Withdrawn EP1860168A3 (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP2006144498A JP2007314636A (ja) 2006-05-24 2006-05-24 粘着シート

Publications (2)

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EP1860168A2 true EP1860168A2 (fr) 2007-11-28
EP1860168A3 EP1860168A3 (fr) 2009-05-20

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Country Status (6)

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US (2) US20070275201A1 (fr)
EP (1) EP1860168A3 (fr)
JP (1) JP2007314636A (fr)
KR (1) KR101068188B1 (fr)
CN (1) CN101077963B (fr)
TW (1) TWI428417B (fr)

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JP6075832B2 (ja) * 2011-10-17 2017-02-08 日東電工株式会社 粘着テープ用フィルムおよび粘着テープ
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KR102113200B1 (ko) * 2017-12-22 2020-06-03 엘씨스퀘어(주) 변형필름을 이용한 전사방법
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Also Published As

Publication number Publication date
TW200804555A (en) 2008-01-16
US20110195250A1 (en) 2011-08-11
US20070275201A1 (en) 2007-11-29
KR101068188B1 (ko) 2011-09-28
TWI428417B (zh) 2014-03-01
CN101077963B (zh) 2011-12-14
JP2007314636A (ja) 2007-12-06
EP1860168A3 (fr) 2009-05-20
CN101077963A (zh) 2007-11-28
KR20070114004A (ko) 2007-11-29

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